How to ask someone on a date

Ladies who lunch. Photo from

Over lunch, my friend Rica shared her distress because she had been indecorously asked out on a date four times in as many weeks. Now, this does not surprise me as she is one of those girls who was blessed with not only beauty and brains, but charm as well.

Rica is a sweet, genuine person, and take my word for it, this is not a case of a “humblebrag”. From the anecdotes, I realised, what we had before us was a breach of social convention that must be addressed. I cannot divulge the details of our conversation. But I can tell you that the ordeal was so awkward that (and I find this funny) my friend won’t be able to show her face at her local greengrocer’s for a while yet.

For those of you out there who need a little help asking someone out on a date, here is The Etiquette Butterfly’s Guide on How to Ask Someone Out. This is written for everyone: whether you are sixteen or sixty, a guy asking a girl he fancies, a guy asking another guy, or a girl asking a guy.

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Get to know the person first
My friend was asked out by a guy who didn’t bother asking for her name first. The saying ‘only after “one thing” comes to mind’.

Find out a little bit about the person you want to ask out. Talk to them first, whether the other person is a work colleague, a casual acquaintance, or if they just happen to catch the same commuter train every day. Learn a little bit about the person, what they like and what they like doing. But don’t go about it as if you are a detective interrogating a suspect; delicacy is what’s required here.

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It’s very rarely the case that a person will go out on a date with a complete stranger. (Speed dating is a case in point. You find out a little bit about someone then you agree to go on a real date or not.) Knowing a little bit about the “object of your desire” serves a purpose: you discover whether you should pursue them further. Value your time and energy as well as theirs by finding out from the start if you share anything in common or if they have character traits you absolutely abhor.
Here is a lighthearted example. Let’s say you are someone who is very optimistic and cheerful. If the other person happens to be extremely sardonic, chances are, the relationship will be short lived, and you won’t remain friends. It’s important to uncover these things before you start dating.

Suave French Guy finds out that he and Taylor Swift share a love for the music of James Taylor before he asked her out. (Clip from Taylor Swift’s Begin Again)

Another reason for getting to know someone before asking them out: you show that you intend to have a meaningful relationship. Generally, people want to feel that they are admired for their substance, abilities, intelligence or personality. Yes, physical attraction plays a very big part in wanting to date someone, but there must be another dimension beyond beauty.

Below is a very short clip from Swan Princess, an animated movie loosely based on Swan Lake. The clip shows Prince Derek declaring that Princess Odette is “beautiful, and all he ever wanted”. When the Princess asks, ‘Is beauty all the matters to you?’ The Prince’s reply leaves a lot to be desired.

Avoid ambiguity
It is better to be exact and unambiguous when asking someone out. Try not to say “hang out”. This can be construed as a group activity or something that might relegate you to the “friend zone” category. Eliminate the loaded description “We’re just hanging out,” later on. If the word “date” is too strong and dated [pun intended] for your modern tastes, opt for “go out” instead.

Be specific
Specify a time or activity that you would like to do together. For example, you can say ‘Would you like to go out with me on Saturday?’ or ‘Are you interested in going wall climbing with me sometime soon?’ This way, the person can subtly indicate whether they reciprocate your interest or not without putting themselves in an awkward position of rejecting you outright.
As well as the coveted ‘Yes, I would,’ they might answer, ‘I’m busy on Saturday, but I’m free on Monday if you want to go out then.’ The same goes for a reply of ‘I’m too scared to go wall climbing, would you like to go ice skating instead?’ Both answers show that they want to go out with you.

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But an answer along the lines of ‘Sorry, I’m busy on Saturday.’ or ‘I don’t like wall climbing,’ without any offer of an alternative indicates they might not return your interest. This puts you in a better position to gauge if they do not want to go out with you.

Saying, ‘Would you like to go out sometime?’ without a specific time or activity leaves the other person but two choices. They will either:
a. Just say ‘Yes’ only to spare your feelings or
b. Say ‘No, thank you,’ thus openly wounding your ego in the process. 

This might create an embarrassing situation from which it is difficult to recover.

Final words
Take courage that in following this guide, asking someone out will not leave either of you feeling uncomfortable or embarrassed. Your chance of success increases when you actually ask.

I am a romantic. I love the whole ritual of dating and courtship. At the risk of sounding overly sentimental, I leave you with the words of the poet John Greenleaf Whittier,

Of all sad words of tongue or pen, the saddest are these, ‘It might have been’.

All the best,

Did you find success by following our guide? We would love to hear your feedback. Please leave a comment below.


One thought on “How to ask someone on a date

  1. Anna

    If a guy contacts me on a Thursday asking what time I finish work on a Friday I get the idea that he might be interested in asking me on a date; however if he’s actually asking me on a date on Thursday I would be inclined to think I’m an after thought… he didn’t have anything better offered. Timing a first date request is equally important


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